Bullz-Eye.com’s Publisher, Gerardo Orlando, caught up with Roeper to discuss the book and Richard’s impressions on all the different kinds of bets he made during that time. As for whether he won or lost money, we won’t spoil it for you. Read the book and enjoy the ride. Every gambler will be able to relate to the stories in the book.

Bullz-Eye: Hi Richard.

Richard Roeper: Hello.

BE: I love the book.

RR: Oh thanks so much.

BE: I’m probably roughly your age and have been gambling for about…well, my whole life. Since I was about ten years old, like you. I think I did my first Vegas trip when I was 18. I lost $120 and thought it was the end of the world.

BE: (laughing) Those red chips were such a big deal back in the day. So I really enjoyed the book, as you hit on a bunch of things that I’ve done throughout my gambling life. But also, you tried a variety of things that I have the same opinion on - stuff that seemed pretty useless but it was fun to read about you giving them a try.

RR: Well thanks.

BE: I’m not going to spoil it for our readers but the Kentucky Derby story, or the several Kentucky Derby stories, were some of the best of the book. Did you bet it again this year?

On distracting other players in Poker: "I’ve certainly seen attractive women really work it. And they don’t have to be overly flirtatious, all they have to do is kind of, you know, bat their eyes and laugh at the jokes and you see guys just bending over backwards not to knock them out. And I’m thinking – “you suckers!"

RR: I did and I did not win. In fact, I believe my horse is just now finishing the race (laughing). But at least there wasn’t as much drama this year. It was a lot of fun. I mean it’s still, as you know, the most exciting two minutes in sports. It’s a great thing to bet on. But I just went with a hunch this year since it was such a wide open field, you know. My horse was Dublin and he came in seventh I think.

BE: Some of the funniest parts of the book were the references to some of the other poker players you played with - the stereotypical, young poker player with the trucker hat, sunglasses, headphones. Talk a little bit about that because we’ve all run into those characters when we’ve played poker.

RR: Well yeah, it’s been about what…six, seven years now since the poker boom really hit, in the early 2000’s. So you know, you get a lot of these young players who, you know they were 14 or 15, watching the World Series of Poker and they have really been influenced by it, to me, in a comical way. Where they see these guys on TV with the sunglasses and the headphones and the Ed Hardy t-shirts and all that stuff. And they all think that they’re the next sensation and they’re so, you know, so serious and…unfortunately, it’s also given a lot of people license to really behave badly, in a boorish manner at the tables. And they don’t get it that if you’re Phil Hellmuth, you get away with it because you’ve got 11 bracelets and you’ve created a persona. If you’re some kid playing at a charity tournament in Chicago, you know, lighten up, get over yourself.

BE: Yeah, it’s hilarious when you run into those guys.

RR: I love messing with them.

BE: One thing I learned, and I haven’t played nearly as much poker as you have, but the persona you take on at the table though does obviously impact your play. There are guys out there who are able to assume this sort of bullying persona and it sometimes works for them pretty well. At least from what I have experienced. But you have played a lot more tournaments than I have.

RR: No, but you’re right Gerardo, it does work. I mean I find myself sometimes at a table thinking “ah, I’ve got to get this guy” and you never should be thinking I’ve got to get this guy. You know, that’s just not what it’s about.

BE: Right.

RR: You can take some personal satisfaction when you do knock somebody out who’s behaving in an obnoxious style, but if he’s got you thinking that way, yeah, it’s working on some level. So one of the things that I try to do is just stay true to my game and not get taken out of a rhythm. There’s also, in addition to people that act in an obnoxious way and try to dominate the tables, there are other approaches. Some people just try to kill you with kindness. They act like they’re your friend and they are like “oh, I hope you and I are at the final table” and that kind of thing. That’s a technique. And I’ve certainly seen attractive women really work it. And they don’t have to be overly flirtatious, all they have to do is kind of, you know, bat their eyes and laugh at the jokes and you see guys just bending over backwards not to knock them out. And I’m thinking – “you suckers!”

BE: (laughing) Oh that’s classic! I guess the lesson though is that you have to strip as much emotion out of it as you can in order to be successful.

RR: You do. And the other thing I have noticed too, having played in the big Vegas tournaments and charity events and stuff like that, when a big name poker player sits at a table, you know somebody that you have seen that’s won bracelets, that’s a well known pro, I mean they can just dominate a table by shear reputation. Nobody wants to mess with these guys. Especially like at the World Series of Poker, the early rounds, these guys…they don’t even have to have a hand. They bet and everybody just folds, folds, folds. Or somebody is so hell bent on saying they knocked out Daniel Negreanu or Mike Matusow that they’ll call anything. And they’re like “oh, I thought I had you” and the guys actually do have hands every once in awhile.

BE: Right.

RR: So they certainly can use their reputations to great, great effect.

BE: Now you seem to enjoy tournament play a lot more. Do you play the poker cash games much in the casinos? I know you play a lot of, or at least in the book, played a lot of cash games online. But do you go to the cash games much in the casinos?

RR: You know, I don’t. First of all, I just prefer the tournament, just the strategy of it, the math of it and just the long term planning of it. But as far as cash games in casinos go, I mean even here in the Chicago area, there’s casinos in northwest Indiana that are close by, and the guys who are playing the cash games there are there every day, grinding it out. And certainly in Vegas they are. And to sit down with them, to me it’s like when you go in to buy a car. You’re buying a car from a guy who sells a car every single day. You’re not going to out bargain the guy. You’re going to think you can…so to me, it’s like walking into any cash game at a big casino - you’re a decided underdog. You’re playing against a bunch of people that do it every single day. So to me, I try to avoid that because you know what? You’re going to lose.

BE: Good point. I enjoyed your list of the best gambling movies and obviously “Rounders” jumped out at me. It came out before the poker craze and it’s such a good movie, really, that captures the whole spirit of Texas hold ‘em.

RR: Yeah. And you’re right, it did come out about five years really before it’s time. I think it influenced a lot of kids who got into poker. But it’s funny because when you look at the timeline, that’s one of the reasons why I think the movie has done much better since then as a home video, you know the DVD, as a cable or a rental or anything, than it did when it came out theatrically. Because even though it had big stars in it, it was a really good movie, it wasn’t a subject that a lot of mainstream people were talking about. The ironic thing is since then, people have tried to do poker movies and most of them have been pretty horrible. Most viewers haven’t even heard of these movies. You know there was a movie called “Deal” that came out with Burt Reynolds and it was just horrible.

BE: (laughing) Another enlightening part of the book was your discussion of the odds of the various games. If you’re going to go out there and have fun gambling, I don’t think the odds should necessarily, you know, drive every decision you make, in terms of what you decide to play. Obviously part of it is the fun factor, what you’re doing with friends, etc. But it’s obviously something you should be aware of and that was definitely helpful. I liked your line about the lottery, which is that you’re really just buying a license to dream for a couple of days, which is so true.

"Poker has affected my appreciation for blackjack because as you know, yeah there’s strategy in blackjack but it’s pretty much you either do it by the book or you take it because you’re feeling it. There’s not a whole lot of variation there so it becomes more of an automatic thing."

RR: Yeah, it is and I think most people get that, at least in the abstract. It’s funny because like in my home newspaper, The Chicago Sun-Times, and this happens at so many companies, there’s a bunch of people who get together every week and buy into the lottery, you know the tickets for the big lucky Friday or whatever.

BE: Right.

RR: And you feel like if you don’t do it, they’re like oh great, they’re going to hit it one day and you’re going to go “all my colleagues are instant millionaires.” So you almost do it out of spite. You’re like, “oh damn it, I’ll give you a buck too because I don’t want to be the idiot.” You know you always hear about the one guy that sues because “well I wanted to be part of the team but…” But yeah, the lottery, it’s beyond a long shot. And everybody always says “well somebody’s got to win” and I’m like “yeah, but it’s not going to be you.”

BE: I was surfing around your blog and your Larry King line was pretty funny.

RR: And it’s even more true, isn’t it, as we speak.

BE: Right. Just for the benefit of our readers, your line was that “a woman in America has better odds of becoming Larry King’s wife than she does of winning the lottery.”

RR: Yeah and that’s mathematically correct. And she’s about ten times more likely to have had slept with tiger Woods than have won the lottery (laughing).

BE: (laughing) So I saw in the book that you played the slots. Has your opinion changed at all about the slots? Or do you get it any more than before? Because I really don’t get it much, other than I know people who like that. That’s just what they do when they go and it’s a casual way to have fun. But boy, I just don’t see it.

RR: I don’t see it on a number of levels. First of all, yeah, it’s also the odds are way against you. The idea that there is some sort of strategy in slots just cracks me up. I know there are slots tournaments and stuff, and I know that there are people that have all their theories, but you know, it’s an unthinking machine with no memory, no matter what people will tell you. They’re not wired to hit at a certain time, they don’t have memory, they don’t go cold and then hot. That’s all people ascribing human virtues to a machine. But on top of all that, it’s just so boring to sit there and to me it’s mind numbing to look at these numbers or patterns, and I don’t care if they are yelling out “Wheel of Fortune” or they have hats smiling at you or whatever it is, it’s still just pressing a button. I don’t get it but people love it. You know when people love the slots, they don’t do anything else, they’ll just play the slots. But as I mentioned in the book, you know you look at any casino layout there are more slots machines than anything else and you can’t go from one thing to another thing without going past slot machines.

BE: Yeah, it’s their biggest breadwinner.

RR: Absolutely.

BE: You play a lot of poker now, so has some of the fun of blackjack gone away? I still really enjoy blackjack when I’m with a group of friends and we take over a table. It’s a great way to pass a lot of time. There is some strategy involved and you can have fun with the table. In the past, I would also go and play blackjack by myself, but now I just don’t really enjoy it as much. Part of it is that the casinos have really played with the odds. I don’t know if you’ve noticed this but they have a lot of single deck games now but then they changed the payout on blackjack and really skewed the odds back in their favor. And now they have replaced a lot of the blackjack tables…I don’t know. The fun of blackjack has gone away for me but I don’t know how you feel about it.

RR: Yeah, I used to go on trips with my buddies to Vegas and we wouldn’t play anything other than blackjack. Maybe a little bit of craps just for that group dynamic again, but it was really about playing blackjack. Where six of us would go, sometimes to the VIP section, sometimes just out in the crowd, and play for 50 or 100 bucks a hand for a couple of hours and have a blast either way, winning or losing. Obviously winning always more fun. And I agree with you. The last time I was out in Vegas I sat down at a single deck table and I don’t know what they paid, six to five or something like that for blackjack. And yeah, after about four hands I actually got up and they were like “sir, you can’t cash out” and I said “of course I can, I’m done.” It was kind of joyless and…yeah, it’s changed a lot. I also think that poker has affected my appreciation for blackjack because as you know, yeah there’s strategy in blackjack but it’s pretty much you either do it by the book or you take it because you’re feeling it. There’s not a whole lot of variation there so it becomes more of an automatic thing. Unless you’re playing with a lot of friends, or sometimes just playing for fun, if I’m out there with a date or something and we’re just playing, she’s playing for 25 bucks or five bucks or whatever, then it can still be fun. But yeah, I don’t play it much anymore.

BE: Yeah, I understand. Though I will say it is fun with a date unless…I had an experience once where she just loved to do whatever she wanted. She wouldn’t listen to the rules and then you’re at one of those tables where you have the jerks who think that she’s destroying their hands. Boy that took a lot of the fun out of it.

RR: Yeah, and you know I get into that a little bit with the book and it’s like there are people that will debate me on this but I keep trying to explain it. Of course it can drive people nuts, but for every mistake she makes that screws your hand, there’s another mistake that she’ll make that will help their hand, and they never mention that.

BE: Absolutely.

RR: And people don’t understand that, they just can’t wrap their minds around that. But I agree, and I don’t want to be at a table if it’s going to make other people upset. So usually, I’ll sit with just friends or just the two of us, you know? If a lot of other people join in, I’ll say “you know, I better just play.” because man, some guys get really upset about those things.

BE: (laughing) The one thing about gambling is it does really bring out the inner assholes sometimes.

RR: You know, I think that’s the thing, it just brings out the true personality. It’s sort of like what they say about drinking. It’s so funny, I’ve got a …one of my friends, whoeven when he’s winning is always like “why didn’t I bet more?” You know, damn, and I’m like - really? He’ll get a blackjack and go “oh, I was betting 300 a hand earlier, now I’m betting 100. I can’t believe I got blackjack.” Okay.

BE: Glass half empty all the time.

RR: Yeah.

BE: You talk a little bit about the mixed messages from the government and it’s sort of a joke how they push the lottery, which is really a terrible bet, and then they don’t let us enjoy a little bit of online poker. Do you think maybe we’re hitting a tipping point on that? I mean Ohio finally approved gambling after years of trying. You’ve got guys like Barney Frank trying to legalize online poker. Are we getting to a point where there’s going to be a tipping point here and people just accept it as more of legitimate way to have fun?

RR: Yeah, I think we’re very close and in some respects we’ve already gotten there. You know, if 12 years ago some kid at MIT told his parents he was going to be a pro poker player, they would be weeping. Now they may not be happy but they also may go “hey, go for it.”

BE: Right.

RR: You now have professional poker players, doing legitimate endorsement deals and showing up at non gambling related events as celebrities. And as far as the government goes, yeah, I think first of all they’re really missing out by not legalizing online poker and getting their cut of it and making it something that’s regulated. I think a lot of people who have their suspicions about some of the online sites would maybe feel better if the government was overseeing it.

BE: I totally agree with you. And just hitting on one more thing from the book, the whole Vegas experience. You told some great stories. Some really fun and then you recounted one miserable experience that you had in Vegas too.

RR: (laughing) Yeah.

BE: Even with all of the other gambling options out there, there’s something about going to Vegas that’s really different from every other experience.

RR: Yeah, it still is to me. I was there about a month or so ago, a month and a half ago, I played in the Wynn Classic Tournament. And yeah, it’s still the ultimate…especially, in the United States in terms of getting away or gambling and just forgetting about everything for two or three days; the whole Vegas experience. That hasn’t diminished for me. You know, I still go out there three, four times a year.

BE: And finally, tell me about the new radio gig.

RR: I’m doing a daily radio show on WLS in Chicago, 2:00-6:00 every afternoon. I had done radio a long time ago actually, before I got into movie reviewing and I kind of missed it. It had been a long time. It’s really fun because I’m still doing movie reviews for my site and for ReelzChannel and all that, but it’s fun to get back to talking about everything from sports to politics to pop culture as well.

BE: Is it something that you guys hope to syndicate out?

RR: Yeah. we’re on the same station that Rush Limbaugh is on and other syndicated hosts so the hope is…and it’s very early because we just started doing it, but so far the numbers are really good and the hope is that we’ll be syndicating the show sooner rather than later. One of the things we do, my co-host is Roe Conn, who’s been doing radio for a long time, and we’re a lot more moderate than the Sean Hannitys and Limbaughs of the world. And there’s a real appetite for that in terms of advertisers and just an audience nationally. You don’t have a lot of syndicated radio shows that present a little more balanced or moderate point of view. So so far, so good.

BE: That makes a lot of sense. I can’t think of one out there that presents a moderate viewpoint.

RR: Pretty much there isn’t, yeah. Air America tried but that was maybe too liberal and we’re not…we have a unique approach Gerardo, we actually have our own opinions about each issue instead of just towing the company line.

BE: Wow, there’s a novel thought!

RR: I know, isn’t it a novel thought? Once in awhile, I think that somebody on the Republican side actually has a good idea. Once in awhile I’ll actually criticize Barack Obama. It’s crazy isn’t it? I know, it’s revolutionary. Independent thought.

BE: Well good luck with the show and again, it’s a great book. And thanks for spending some time with us.